关于青霉硫呋醇的合成研究：一种高级螺环二酮哌嗪中间体的合成。
Synthetic studies towards the penicisulfuranols: Synthesis of an advanced spirocyclic diketopiperazine intermediate.
作者信息
Gayler Kevin M, Lambert Kyle M, Wood John L
机构信息
Department of Chemistry and Biochemistry, Baylor University, Waco, TX, 76798, USA.
出版信息
Tetrahedron. 2019 Jun 14;75(24):3154-3159. doi: 10.1016/j.tet.2019.01.032. Epub 2019 Jan 21.
Abstract
The 2,5-diketopiperazine (DKP) moiety is a core feature of many natural products and medicinally relevant scaffolds. As part of our efforts directed towards a total synthesis of penicisulfuranol B, we have developed and report herein: (1) the preparation of an diketopiperazine intermediate accessible via a molybdenum-mediated oxidation of a parent diketopiperazine, and (2) further synthetic studies leading to a novel spirocyclic dihydrobenzofuran-containing diketopiperazine.
摘要
2,5-二酮哌嗪（DKP）部分是许多天然产物和具有药用价值的骨架的核心特征。作为我们全合成青霉硫呋醇B工作的一部分，我们在此开发并报告：（1）通过钼介导的母体二酮哌嗪氧化制备一种二酮哌嗪中间体，以及（2）进一步的合成研究，得到一种含新型螺环二氢苯并呋喃的二酮哌嗪。
相似文献
1
Synthetic studies towards the penicisulfuranols: Synthesis of an advanced spirocyclic diketopiperazine intermediate.关于青霉硫呋醇的合成研究：一种高级螺环二酮哌嗪中间体的合成。
Tetrahedron. 2019 Jun 14;75(24):3154-3159. doi: 10.1016/j.tet.2019.01.032. Epub 2019 Jan 21.
2
Diastereoselective Spirocyclization: Entry to Spirocyclic Diketopiperazines.非对映选择性螺环化反应：通往螺环二酮哌嗪类化合物的途径。
Org Lett. 2023 Nov 3;25(43):7822-7826. doi: 10.1021/acs.orglett.3c03031. Epub 2023 Oct 19.
3
Total synthesis of complex 2,5-diketopiperazine alkaloids.复杂的 2,5-二酮哌嗪类生物碱的全合成。
Alkaloids Chem Biol. 2023;90:159-206. doi: 10.1016/bs.alkal.2023.06.002. Epub 2023 Aug 7.
4
The expanding spectrum of diketopiperazine natural product biosynthetic pathways containing cyclodipeptide synthases.含环二肽合成酶的二酮哌嗪天然产物生物合成途径的不断扩大。
Org Biomol Chem. 2019 Feb 27;17(9):2305-2314. doi: 10.1039/c8ob03063d.
5
Synthesis of proline-based diketopiperazine scaffolds.基于脯氨酸的二酮哌嗪支架的合成。
J Org Chem. 2009 Jun 5;74(11):4267-71. doi: 10.1021/jo9004876.
6
Cyclic RGD peptidomimetics containing bifunctional diketopiperazine scaffolds as new potent integrin ligands.含双功能二酮哌嗪支架的环 RGD 肽模拟物作为新型有效的整合素配体。
Chemistry. 2012 May 14;18(20):6195-207. doi: 10.1002/chem.201200457. Epub 2012 Apr 19.
7
A facile synthesis of cysteine-based diketopiperazine from thiol-protected precursor.一种由硫醇保护的前体轻松合成基于半胱氨酸的二酮哌嗪。
R Soc Open Sci. 2018 Jun 20;5(6):180272. doi: 10.1098/rsos.180272. eCollection 2018 Jun.
8
One-pot synthesis and sigma receptor binding studies of novel spirocyclic-2,6-diketopiperazine derivatives.新型螺环-2,6-二酮哌嗪衍生物的一锅法合成及σ受体结合研究
Bioorg Med Chem Lett. 2016 Jun 1;26(11):2676-9. doi: 10.1016/j.bmcl.2016.04.010. Epub 2016 Apr 6.
9
Total Syntheses of Herqulines B and C.赫奎琳 B 和 C 的全合成。
J Am Chem Soc. 2019 Feb 27;141(8):3409-3413. doi: 10.1021/jacs.8b13849. Epub 2019 Feb 18.
10
Nano-pulsed discharge plasma-induced abiotic oligopeptide formation from diketopiperazine.纳米脉冲放电等离子体诱导二酮哌嗪形成非生物寡肽。
Naturwissenschaften. 2022 Jun 10;109(4):33. doi: 10.1007/s00114-022-01803-y.
引用本文的文献
1
The Cytotoxic Activity of Secondary Metabolites from Marine-Derived spp.: A Review (2018-2024).海洋来源的[具体物种]次生代谢产物的细胞毒性活性综述（2018 - 2024年）
Mar Drugs. 2025 Apr 30;23(5):197. doi: 10.3390/md23050197.
2
A Ring Expansion Approach To -oxy-2,5-diketopiperazines.一种合成-氧代-2,5-二酮哌嗪的扩环方法。
Tetrahedron Lett. 2022 Jun 8;99. doi: 10.1016/j.tetlet.2022.153851. Epub 2022 May 18.
本文引用的文献
1
A Three-Step Entry to the Aspirochlorine Family of Antifungal Agents.进入抗真菌剂阿斯匹氯林家族的三步途径。
Angew Chem Int Ed Engl. 2000 Nov 3;39(21):3866-3868. doi: 10.1002/1521-3773(20001103)39:21<3866::AID-ANIE3866>3.0.CO;2-E.
2
Penicisulfuranols A-F, Alkaloids from the Mangrove Endophytic Fungus Penicillium janthinellum HDN13-309.青霉硫呋喃醇A - F，来自红树林内生真菌产黄青霉HDN13 - 309的生物碱
J Nat Prod. 2017 Jan 27;80(1):71-75. doi: 10.1021/acs.jnatprod.6b00483. Epub 2016 Dec 19.
3
Synthesis and activity evaluation of the cyclic dipeptides arylidene N-alkoxydiketopiperazines.环二肽亚芳基 N-烷氧基二酮哌嗪的合成与活性评价
Bioorg Med Chem. 2016 Nov 1;24(21):5197-5205. doi: 10.1016/j.bmc.2016.08.038. Epub 2016 Aug 24.
4
The flavan-isoflavan rearrangement: bioinspired synthetic access to isoflavonoids via 1,2-shift-alkylation sequence.黄烷-异黄烷重排：通过1,2-迁移-烷基化序列实现对异黄酮类化合物的仿生合成途径。
Chem Commun (Camb). 2015 Apr 25;51(32):7012-4. doi: 10.1039/c5cc01572c. Epub 2015 Mar 24.
5
Novel piperazinediones as antitumor agents.新型哌嗪二酮类化合物作为抗肿瘤药物。
Anticancer Res. 2014 Aug;34(8):4013-9.
6
Convergent synthesis and structural confirmation of phellodonin and sarcodonin ε.汇聚合成与对树舌素和辛可尼丁 ε 的结构确证。
Org Lett. 2013 May 3;15(9):2080-3. doi: 10.1021/ol400709f. Epub 2013 Apr 11.
7
Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family.基于合成指导的肌蛤菌素、石耳菌素和齿孔菌素天然产物家族的结构修正。
J Org Chem. 2011 Feb 18;76(4):1013-30. doi: 10.1021/jo102228j. Epub 2011 Jan 20.
8
Concise and diversity-oriented route toward polysubstituted 2-aminoimidazole alkaloids and their analogues.通向多取代2-氨基咪唑生物碱及其类似物的简洁且以多样性为导向的路线。
Angew Chem Int Ed Engl. 2010 Dec 3;49(49):9465-8. doi: 10.1002/anie.201004256.
9
Structural and biochemical characterization of the cytochrome P450 CypX (CYP134A1) from Bacillus subtilis: a cyclo-L-leucyl-L-leucyl dipeptide oxidase.枯草芽孢杆菌细胞色素 P450 CypX（CYP134A1）的结构和生化特性：环-L-亮氨酰-L-亮氨酸二肽氧化酶。
Biochemistry. 2010 Aug 31;49(34):7282-96. doi: 10.1021/bi100910y.
10
Hydrogen bonding lowers intrinsic nucleophilicity of solvated nucleophiles.氢键作用降低了溶剂化亲核试剂的固有亲核性。
J Am Chem Soc. 2008 Nov 12;130(45):15038-46. doi: 10.1021/ja802814a. Epub 2008 Oct 18.
Zotero 插件